2-Fluoro-6-methoxybenzaldehyde → (R)-5-(5-(1-(2-fluoro-6-methoxybenzyl)piperidin-3-yl)-1-methyl-1H-1,2,4-triazol-3-yl)-3-(pyridin-4-yl)-1H-indazole

HRID 1465707ノート

反応式

HRID 1465707 の反応式
[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH3:11])[C:3]=1[CH:4]=O.[CH3:12][N:13]1[C:17]([C@@H:18]2[CH2:23][CH2:22][CH2:21][NH:20][CH2:19]2)=[N:16][C:15]([C:24]2[CH:25]=[C:26]3[C:30](=[CH:31][CH:32]=2)[NH:29][N:28]=[C:27]3[C:33]2[CH:38]=[CH:37][N:36]=[CH:35][CH:34]=2)=[N:14]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CO.C(Cl)Cl.O>[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH3:11])[C:3]=1[CH2:4][N:20]1[CH2:21][CH2:22][CH2:23][C@@H:18]([C:17]2[N:13]([CH3:12])[N:14]=[C:15]([C:24]3[CH:25]=[C:26]4[C:30](=[CH:31][CH:32]=3)[NH:29][N:28]=[C:27]4[C:33]3[CH:34]=[CH:35][N:36]=[CH:37][CH:38]=3)[N:16]=2)[CH2:19]1

参加物

7

反応物 3

HCID 27373572-Fluoro-6-methoxybenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 86695582(R)-5-(1-methyl-5-(piperidin-3-yl)-1H-1,2,4-triazol-3-yl)-3-(pyridin-4-yl)-1H-indazole

生成物 1

HCID 56971413(R)-5-(5-(1-(2-fluoro-6-methoxybenzyl)piperidin-3-yl)-1-methyl-1H-1,2,4-triazol-3-yl)-3-(pyridin-4-yl)-1H-indazole収率 63.6%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

Added 2-Fluoro-6-methoxy benzaldehyde (20 mg, 0.129 mmol) to a solution of (R)-5-(1-methyl-5-(piperidin-3-yl)-1H-1,2,4-triazol-3-yl)-3-(pyridin-4-yl)-1H-indazole (15 mg, 0.0379 mmol) and sodium triacetoxyborohydride (25 mg, 0.118 mmol) in MeOH (4 ml) at room temperature, then stirred for 2 hours. Reaction was diluted with CH2Cl2 (50 ml) and H2O (25 ml), organic layer was separated, dried over Na2SO4, filtered and solvent evaporated. The residue was chromatographed on silica gel eluting with 5% v/v MeOH/CH2Cl2/NH4OH to yield (R)-5-(5-(1-(2-fluoro-6-methoxybenzyl)piperidin-3-yl)-1-methyl-1H-1,2,4-triazol-3-yl)-3-(pyridin-4-yl)-1H-indazole as a white solid (12 mg).

後処理

  1. customReaction
  2. customwas separated
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customsolvent evaporated
  6. customThe residue was chromatographed on silica gel eluting with 5% v/v MeOH/CH2Cl2/NH4OH

出典と根拠

ORDレコード
ord-b48628639f43466bb4eb1c57bfb8aa56
出典データセット
uspto-grants-2015_04
特許番号
US08999966B2

反応ノート

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